Undercover Amusements
by MerlinWinchestr
Summary: Annalee has seen a lot of strange things in her life, but Will Pinkerton and Kate Warne take the cake. Especially when they're undercover.


**Welcome to my first story for the amazing show, _The Pinkertons._ I hope you enjoy both this and the stories to follow. Being a historian and a lover of all things 1860s, I'm going to use this fandom as a way to combine my historical knowledge and research skills with my writing, so check out the bottom of the page for historical notes and research that went into this story.  
**

 **Category: Gen  
Setting: pre-1x22  
Characters/Pairings: Annalee Webb, Will Pinkerton, Kate Warne.  
Rating/Warnings: K+.  
Summary: ****Annalee has seen a lot of strange things in her life, but Will Pinkerton and Kate Warne take the cake. Especially when they're undercover.**

 **Disclaimer: If you recognize it, I don't own it.**

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Undercover Amusements

Kansas City, Missouri was not a small town. Situated right on the edge of the western expansion of the United States, people drifted in and out of Kansas City every day. With many different boarding options throughout the city, both permanent and temporary, it was easy for people to come and go without being noticed. There were the regulars, of course, the permanent or nearly permanent residents who frequented the same establishments day after day.

As proprietor of the DuBois Hotel, Annalee Webb was used to seeing both strangers and regulars in the bar portion of her business. Most of her regulars had their daily habits. Ezra Warren, for example, stopped by every day at exactly 5:15 in the afternoon to drink a beer with Hector Bailey for thirty minutes before each man went home to their wives. Other regulars, however, liked to keep her on her toes, those regulars mostly being Will Pinkerton and Kate Warne.

Kate had caught her by surprise almost from the very beginning. She came in one day with brown hair and a modest every day dress, and the next she came in with blonde hair and a pink dress that could only be described as stereotypical southern belle. Annalee had been preparing to go and ask what brought on the change, when Will had stumbled in with a man she thought she recognized but couldn't place. She had nearly dropped the beer she was bringing over when she heard Kate speaking in a thick southern accent. Deciding that somethings were better left unasked, Annalee ignored the incident and carried on like it was a normal day.

It wasn't until a few weeks later when Will trudged in wearing a ridiculous bowtie and the very epitome of a dandy outfit that Annalee had to ask. "Undercover." Will had mumbled in reply and quickly drowned his second whiskey before walking out with barely a goodbye. Annalee watched him go, surprised at the answer. In retrospect, it made sense. As Pinkerton agents, it would be necessary for both Kate and Will to go undercover and pretend to be someone they weren't in order to get the information they needed.

That didn't mean the two agents didn't still catch her and the other patrons by surprise. The regulars of the DuBois had quickly gotten accustomed to the Pinkertons showing up in a wide variety of personas. More often than not, they found it more amusing then the everyday happenings of the town. While they made it appear that they weren't, everyone in the DuBois had learned to listen in and hide their laughter at whatever personas Kate and Will had assumed.

Several of the men had started making bets on what accent the two agents would be using that day. The betting had carried over to her girls, but Annalee had never participated. Not that she didn't want too; she just figured that it wouldn't look good for the proprietor to be taking all of her patron's and worker's money on bets instead of product. She knew Kate and Will better than most, and it was fairly simple to guess what accent the two were likely to use, especially since Will seemed to favor a southern accent.

Annalee had secretly worried that having the two Pinkertons frequenting the DuBois would be bad for business. On the contrary, however, business had never been better, especially after it had become known that entertainment could be found in the undercover antics of Will Pinkerton and Kate Warne. Annalee was half-tempted to start charging an admittance fee as if she was running a theater on top of everything else. Other times she was tempted to start charging the two Pinkertons for damages done in the many, many fights that just seemed to follow them.

Taking a deep breath, Annalee sent a quick prayer that tonight would be one of the ticket selling nights as Will practically dragged a portly man up to the bar. He flashed her a grin, and she raised her eyebrows as she took in his appearance, most notably the green and black kilt and knee-high socks.

"Ah, Annalee, how bou' pourin' us a drink or two, my dear?" the thick Scottish accent caught her by surprise, but she managed to catch herself before blowing his cover.

"Of course." She smiled and turned to grab two mugs of beer.

It was all she could do to keep from laughing as she poured the drinks and listened to Will blabber on about some land for sale across the Kansas border in that accent. She couldn't help but think about how similar he sounded to his father, though she would wisely keep that thought to herself. If there was anything that could sour Will, it was being compared to his father.

"Ah, thank ye dearie." Will grinned and gave her a wink before turning his attention back to his mark.

As she turned back to the bar, she noticed a couple of regulars sitting near Will turning their backs to hide their laughter. She could hear the chuckling throughout the bar though. Hiding her own laughter, Annalee had to admit, this persona took the cake and she was never going to let Will live it down. Turning back to glance at Will once more, she grinned. Oh yeah, he was never going to hear the end of this one.

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Historical Notes

 **This website will not allow me to provide a direct link to my source used, so if you would like to click on a direct link, please check out this story on my Ao3 account (I am MerlinWinchestr on there as well), or use the titles provided to Google Search. Sorry for the inconvenience.  
**

*Despite how it appears in the show, Kansas City, Missouri was not a small town. The population of Kansas City in 1860 was 4,418. By 1870, the population had increased to 32,260. While I could not find the exact population for 1865 when the show is set, I would assume it would be between these two numbers with the permanent residence growing steadily throughout the years.  
 _Source_ : _The Encyclopedia Britannica, 11th edition, Kansas City, MO edition, page 662. (This book can be found on archive . o r g).  
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